title: Synthesis of α-L-threose nucleoside phosphonates via regioselective sugar protection.
abstract: A new synthesis route to α-L-threose nucleoside phosphonates via 2-O and 3-O selectively protected L-threose is developed. The key intermediates 2-O-benzoyl-L-threonolactone and 1-O-acetyl-2-O-benzoyl-3-O-t-butyldiphenylsilyl-L-threofuranose were functionalized to synthesize 2'-deoxy-2'-fluoro- and 3'-C-ethynyl L-threose 3'-O-phosphonate nucleosides. The key intermediates developed are important intermediates for the synthesis of new L-threose-based nucleoside analogues, TNA phosphoramidites, and TNA triphosphates.
authors.affiliation: Laboratory of Medicinal Chemistry, Rega Institute for Medical Research, KU Leuven, Minderbroedersstraat 10, 3000 Leuven, Belgium.
authors.forename: Shrinivas G
authors.initials: SG
authors.lastname: Dumbre
authors.forename: Mi-Yeon
authors.initials: MY
authors.lastname: Jang
authors.forename: Piet
authors.initials: P
authors.lastname: Herdewijn
mesh_terms: D002241:Carbohydrates / Q000737:chemistry*; D008968:Molecular Conformation; D009705:Nucleosides / Q000138:chemical synthesis* / Q000737:chemistry; D063065:Organophosphonates / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism; D013780:Tetroses / Q000138:chemical synthesis* / Q000737:chemistry
chemical_list: D002241:Carbohydrates; D009705:Nucleosides; D063065:Organophosphonates; D013780:Tetroses; C073321:erythrose